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ABO 2,7,8-Trioxabicyclo3.2.1octyl Ac Acetyl ACBZ 4-Azidobenzyloxycarbonyl ACE -Chloroethoxycarbonyl AcHmb 2-Acetoxy-4-methoxybenzyl Acm Acetamidomethyl Ad 1-Adamantyl Adoc 1-Adamantyloxycarbonyl Adpoc 1-(1-Adamantyl)-1-methylethoxycarbonyl AIBN 2,2-Azobis(2-methylpropionitrile) or Azobisisobutyronitrile All Allyl Alloc Alloxycarbonyl Als Allylsulfonyl AMB 2-(Acetoxymethyl)benzoyl AN 4-Methoxyphenyl or anisyl Anpe 2-(4-Acetyl-2-nitrophenyl)ethyl AO Atomic orbital AOC Allyloxycarbonyl p-AOM p-Anisyloxymrthyl or (4-methoxyphenoxy)methyl Ar Aryl atm Atmosphere ATP Adenosine 5-triphosphate ATPase Adenosinetriphosphatase Azb p-Azidobenzyl Bam Benzamidomethyl BBA Butane-2,3-bisacetal BBn p-Bromobenzyl 9-BBN 9-Borabicyclo3.3.1nonane BDMS Biphenyldimethylsilyl BDT 1,3-Benzodithiolan-2-yl Bic 5-Benzisoxazolymethoxycarbonyl Bmpc 2,4-Dimethylthiophenoxycarbonyl Bmpm 1,1-Bis(4-methoxyphenyl)-1-pyrenylmethyl BMS Borane-methyl sulfide Bn Benzyl BOC t-Butylcarbonyl t-BOC t-Butylcarbonyl BOM Benzyloxymethyl BOP Benzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate BOP-Cl N,N-Bis(2-oxo-3-oxazolidinyl)phosphinic bp Boiling point Bpoc 1-methyl-1-(4-biphenyl)ethoxycarbonyl Bpy 2,2-Bipyridyl br Broad (spectral) BSA Bistrimethylsilyl acetamide Bt Benzotriazo-1-yl or 1-benzotriazolyl BTBA Benzyltributylammonium chloride Bu Butyl s-BU Sec-Butyl t-Bu tert-Butyl Bum t-Butoxymethyl t-Bumeoc 1-(3,5-Di-t-butylphenyl)-1-methylethoxycarbonyl Bz Benzoxyl oC Degree Celsius calcd Calculated Cam Carboxyamidomethyl cAMP Adenosine cyclic 3,5-phosphate CAN Cerium(IV) ammonium nitrate Cbz Benzyloxycarbonyl CD Circular dichrosim CDI 1,1-Carbonyldiimidazole Cee 1-(2-Chloroethoxy)ethyl CI Chemical ionization (in MS) Configuration interaction (in MO theory) CIDNP Chemically induced dynamic nuclear polarization cm Centmeter CMPI 2-Chloro-1-methylpyridium chloride CNDO Complete neglect of differential overlap Coc Cinnamyloxycarbonyl COD 1,5-Cyclooctadiene concd Concentrated COSY Correlation spectroscopy COT Cyclooctatetrene Cp Cyclopentadienyl CPTr 4,4,4”-Tris(4,5-dichlorophthalimido)riphenylmethyl CSA Camphorsulfonic acid CTMP 1-(2-Chloro-4-methyl)phenyl-4-methoxypiperidin-4-yl Cys Cysteine Chemical shift in ppm d Day, doublet (spectral) DABCO 1,4-Diazabicyclo2.2.2octane DAM Di(4-methoxyphenyl)methyl DAST Diethylaminosulfurtrifluoride DB-t-BOC 1,1-Dmethyl-2,2-dibromoethoxycarbonyl DBD-Tmoc 2,7-Di-t-butyl9-(10,10-dioxo-10,10,10,10-tetrahydrothioxanthyl)methy lcarbonyl DBN 1,5-Diazabicyclo4.3.0non-5ene DBU 1,8-Diazabicyclo5.4.0undec-7-ene DCC Dicyclohexylcarbodiimide DCMME Dichloromethylammonium chloride DDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone de Diastereomeric excess DEAD Diethylazodicarboxylate DEIPS Diethylisopropylsilyl DEPT Distortionless enhancement by polarization transfer DG Diacyl glycerol DIAD Diisopropyl azodicarboxylate DIBAH Diisobutylalumium hydride DIBAL Diisobutylaluminum hydride Dim 2-(1,3-Dithianyl)methyl DIPEA Diisopropylethylamine DIPT Diisopropyl tartrate DMAC Dimethylacetamide DMAD Diethyl acetylenedicarboxylate DMAP 4-Dimethylaminopyridine DME Dimethoxyethane DMF N,N-Dimethylformamide DMIPS Dimethylisopropylsilyl Dmoc Dithianylmethoxycarbonyl DMP Dimethylpropane Dmp Dimethylphosphinyl DMPM 3,4-Dimethoxybenzyl DMPU 1,3-Dimethyl-3,4,5,6-tetrhydro-2(1H)-pyrimidinone DMS Dimethyl sulfate DMSO Dimethyl sulfoxide or methyl sulfoxide DMT Dimethoxytrityl DMTr Di(p-methoxyphenyl)phenylmethyl DNA Deoxyribonucleic acid DNB p,p-Dinitrobenzhyrryl DNMBS 4-(4,8-Dimethoxynaphthylmethyl)benzenesulfonyl DNP 2,4-Dinitrophenyl Dobz p-(Dihydroxyboryl)benzyloxycarbonyl DPM Diphenylmethyl DPMS Diphenylmethylsilyl Dpp Diphenylphosphinyl DPPA Diphenylphosphoryl azide Dppe 2-(Diphenylphosphino)ethyl Dppm (Diphenyl-4-pyridyl)methyl Dpt Diphenylthiophosphinyl DTBMS Di-t-butylsilylene Dts Dithiasuccinimidyl E1 Unimolecular elimination E2 Bimolecular elimination ED50 Dose that is effective in 50% of test subjects EDC 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide EDTA Ethylenediaminetetraacetic acid EE 1-Ethoxyethyl ee Enantiomeric excess EI Electron impact (in MS) ESR Electron spin resonance Et Ethyl FAB Fast atom bombardment (in MS) Fcm-NR2 N-Ferrocenylmethyl FD Field distortion (in MS) FG Founctional group FID Flame ionization detection or Free induced decay (in NMR) Fm 9-Fluorenylmethyl FMOC 9-Fluorenylmethylcarbamate Fp 5 FT Foutier transform g Gram GC Gas chromatography GTP Guanosine 5-triphosphate GUM Guaiacolmethyl h Hour HCA Hexachloroacetone Hex Hexyl HMDS 1,11,3,3,3-Hexamethyldisilazane HMO Huckel molecular orbital HMPA Hexamethylphosphoramide HMPT Hexamethylphosphoroustriamide HOBT 1-Hydroxybenzotriazole HOMO Highest occupied molecular orbital HPLC High performance liquid chromatography HRMS High-resolution mass spectrum h Irradiation with light Hz Hertz hZ Homobenzyloxycarbonyl ICR Ion cyclotron resonance IDTr 3-(Imidazole-1-ylmethyl)-4,4”-dimethoxytriphenylmethyl Im Imidazole-1-yl or 1-imidazolyl iMds 2,6Dimethoxy-4-methylbenzenesulfonyl INDO Incomplete neglect of differential overlap IP Ionization potential Ipaoc 1-Isopropylallyloxycarbonyl IPDMS Isopropyldimethylsilyl IR Infrared J Coupling constant (in NMR) k Kilo KAPA Potassium 3-aminopropylamide KHMDS Potassium bis(trimethylsilyl)amide or potassium hexamrthyldisilane L Triphenylphosphine ligand or liter LAH Lithium aluminum hydride LCAO Linear combination of atomic orbitals LDA Lithium diisopropylamide LDBB 4,4-Di-tert-butyybiphenyl ylide Lev Levulinoyl LevS Levulinoyldithioacetal ester 4,4-(ethylenedithio)pentanoyl LFER Linear free energy relationship LICA Lithium isopropylcyclohexylamide LHMDS Lithium bis(trimethylsilyl)amide or lithium hexamrthyldisilane LTA Lead tetraacetate LTMP Lithium 2,2,6,6-tetramethylpiperidide LUMO Lowest unoccupied molecular orbital Micro m Multiple (spectral), meter, milli M Moles per liter or mega MAD Methylaluminum bis(2,6-di-t-butyl-4-methylphenoxide MBE 1-(Methyl-1-benzyloxyethyl MBF 2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran2-yl MBS p-Methoxybenzenesulfonyl MCPBA m-Chloroperbenzoic acid Mds 2,6-Dimethyl-4-methoxybenzenesulfonyl m/e Mass to charge ratio (in MS) MEM -Methoxyethoxymethyl MeOZ p-Methoxybenzyloxycarbonyl Mes Mesityl 2,4,6-trimethylphenyl MHz Megahertz min Minute MINDO Modified intermediate neglect of differential overlap mM Millimoles per liter MMTr p-Methoxyphenyldiphenylmethyl MO Molecular orbital mol Mole MOM Methoxymethyl MoOPH Oxodiperoxymolybdenum(pyridine) hexamethylphosphoramide Moz p-Methoxybenzyloxycarbonyl mp Melting point MPM p-Methoxyphenylmethyl or p-Methoxybenzyl Mps p-Methoxyphenylsufonyl Mpt Dimethylthiophosphinyl mRNA Messenger RNA Ms Methanesulfonyl or mesyl MS Mass spectrometry MSA Methanesulfonic acid Msib 4-(Methylsulfinyl)benzyl Msz 4-Methylsulfinylbenzyloxycarbonyl Mtb 2,4,6-Trimethoxybenzenesufonyl Mte 2,3,5,6-Tetramethyl-4-methoxybenzenesulfonyl MTHP 4-Methoxytetrahydropyranyl MTM Methylthiomethyl MTMB 4-(methylthiomethoxy)butyryl MTMECO 2-(Methylthiomethoxy)ethoxycarbonyl MTMT 2-(Methylthiomethoxymethyl)benzoxy Mtpc 4-Methylthiophenoxycarbonyl Mtr 2,3,6-Trimethyl-4-methoxybenzenesulfonyl Mts 2,3,6-Trimethylbenzenesulfonyl(mesitylenesulfonyl) m/z Mass to charge ratio (in MS) n nao NAD Nicotinamide adenine dinucleotide NADH Reduced NAD NBA N-Bromoacetamide NBS N-Bromosuccinimide NCS N-Chlorosuccinimide Ni(acac)2 Nickel acetylacetonate NIS N-Iodosuccinimide Ni(R) Raney Nickel NMM N-Methyl morpholine NMR Nuclear magnetic resonance Noc 4-Nitrocinnamyloxycarbonyl NOE Nuclear Overhauser effect NOESY Nuclear Overhauser effect spectroscopy NPS 2-Nitrophenylsulfenyl Npys 3-Nitro-2-pyridinesulfenyl Nu Nucleophile OD Optical density ONB o-Nitrobenzyl ORD Optical rotary dispersion ot Oven temperature PADA Potassium azodicarboxylate PCC Pyridinium chlorochromate PDC Pyridinium dichromate PdCl2(tpp)2 Dichlorobistris(2-methylphenyl)phosphinepalladium Pd2(dba)3 Tris(dibenzylideneacetone)dipalladium PE Photoelectron Peoc 2-Phosphonioethoxycarbonyl or 2-(Triphenylphosphonio)ethoxycarbonyl Pet 2-(2-Pyridyl)ethyl PG Protective group Ph Phenyl Phenyl Phen 1,10-Phenanthroline Phenoc 4-Methoxyphenacyloxycarbonyl Phth Phthaloyl Pixyl 9-(9-Phenyl)xanthenyl PMB p-Methoxybenzyl PMBM p-Methoxybenzoxymethyl Pmc 2,2,5,7,8-Pentamethylchroman-6-sulfonyl Pme Pentamethylbenzenesulfonyl PMS p-Methylbenzylsulfonyl PNB p-Nitrobenzoyl PNBSP p-Nitrobenzenesulfonyl peroxide POM 4-Pentenyloxymethyl or Pivaloxymethyl PPA Polyphosphoric acid PPE Polyphosphate ester ppm Parts per mollion Ppoc 2-Triphenylphosphonioisopropoxycarbonyl PPTS Pyridinium p-to;uenesulfonate Pr Propyl i-Pr Isopropyl Psec 2-(Phenylsulfonyl)ethoxycarbonyl PTM Phenylthiomethyl PTC Phase-transfer catalysis Pv Pivaloyl Py Pyridine Pyoc 2-(2- and 4-pyridyl)ethoxycarbonyl q Quartet Rf Retention factor rRNA Ribosomal RNA rt Room temperature s Singlet or second Scm S-Carboxymethylsulfenyl ScmCl Methoxycarbonylsulfenyl chloride SEM Trimethylsilylmeyhoxyethyl SES -Trimethylsilylethanesulfonyl SET Single electron transfer SMOM (Phenyldimethylsilyl)methoxymethyl SN1 Unimolecular nucleophilic substitution SN2 Bimolecular nucleophilic substitution SN Nucleophilic substitution with allylic rearrangement Snm S-(N-Methyl-N-phenylcarbamoyl)sulfenyl STABASE 1,1,4,4-Tetramethyldisilyl azacyclopentane Su Succinimidyl t Triplet Tacm Trimethylacetamidomethyl TBAF Tetrabutylammonium fluoride TBAI Tetrabutylammonium iodide TBDMS t-Butyldimethylsilyl TBDPS t-Butyldiphenylsilyl TBDS Tetra-t-butoxydisiloxane-1,3-diylidene TBHP t-Butyl hydroperoxide TBMPS t-Butylmethoxyphenylsilyl TBS Tributylsilane TBTr 4,4-4”-Tris(benzyloxy)triphenylmethyl TcBoc 1,1-Dimethyl-2,2,2-trichloroethoxycarbonyl TCNE Tetracyanoethylene TCNQ 7,7,8,8-Tetracyanoquinodimethane Tcroc 2-(Trifluoromethyl)-6-chromonylmethylene carbonyl Tcrom 2-(Trifluoromethyl)-6-chromonylmethylene TDS Thexyldimethylsilyl TEA Triethylamine TEAB Tetraethylammonium bromide TEBAC Benzyltriethylammonium chloride Tebbs TED Triethylene diamine Teoc 2-(Trimethylsilyl)e
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